Cheap flights from Key West (EYW) to Chicago (CHI) from $207
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/25. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
EYW — CHI
מאי 19 — מאי 261
From?
To?
1 adult, Economy
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Cheap flight deals from Key West to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated מאי 14, 2024.
Popular in | November |
|---|---|
Cheapest in | October |
Average price | $437 |
Round-trip from | $223 |
What is the cheapest day to fly round-trip from Key West to Chicago?
Monday is generally a great day to depart. Flying on this day could help you save up to 43%.
What is the cheapest month to fly from Key West to Chicago?
October can be a great time to fly to Chicago from Key West with a flight ticket averaging about $373. Cheapflights users have found deals in the month of October for as cheap as $227. The most expensive prices can be found in the month of November.
When is the cheapest time to fly from Key West to Chicago (EYW - CHI)?
A simple way to save on the total cost of your ticket is to fly from Key West to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 34% on your trip compared to booking a flight in the afternoon.
Cheap United Airlines flights from Key West to Chicago
Explore cheap flight options specifically provided by United Airlines for the route between Key West and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Find some of the cheapest United Airlines flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.
ד' 11/64:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
א' 11/1010:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/14$229
ד' 11/61:00 pmEYW - ORD
1 stop9h 23mUnited Airlines
א' 11/1010:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/14$259
א' 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
א' 8/257:35 amORD - EYW
1 stop25h 20mUnited Airlines
Deal found 5/14$445
ד' 11/61:00 pmEYW - ORD
1 stop9h 23mUnited Airlines
א' 11/107:35 amORD - EYW
2 stops11h 00mUnited Airlines
Deal found 5/14$493
א' 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
א' 8/259:15 pmORD - EYW
2 stops15h 54mUnited Airlines
Deal found 5/14$495
ה' 6/2011:20 amEYW - ORD
2 stops21h 28mUnited Airlines
ב' 6/246:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Deal found 5/14$552
ה' 6/203:20 pmEYW - ORD
2 stops9h 53mUnited Airlines
ב' 6/246:40 pmORD - EYW
1 stop18h 55mUnited Airlines
Deal found 5/14$585
ב' 5/2011:45 amEYW - ORD
1 stop28h 08mUnited Airlines
ב' 5/276:30 amORD - EYW
2 stops12h 05mUnited Airlines
Deal found 5/14$614
א' 8/1811:20 amEYW - ORD
2 stops12h 13mUnited Airlines
א' 8/259:15 pmORD - EYW
2 stops15h 54mUnited Airlines
Deal found 5/14$680
Cheap American Airlines flights from Key West to Chicago
Explore cheap flight options specifically provided by American Airlines for the route between Key West and Chicago. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Browse through some of the cheapest American Airlines flights traveling from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.
ד' 11/63:16 pmEYW - ORD
1 stop5h 17mAmerican Airlines
א' 11/107:00 amORD - EYW
1 stop7h 09mAmerican Airlines
Deal found 5/14$345
ה' 6/204:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
ב' 6/245:01 amORD - EYW
1 stop7h 54mAmerican Airlines
Deal found 5/14$347
ב' 5/206:10 pmEYW - ORD
1 stop6h 49mAmerican Airlines
ב' 5/275:15 amORD - EYW
1 stop4h 46mAmerican Airlines
Deal found 5/14$435
ה' 6/2712:46 pmEYW - ORD
2 stops9h 10mAmerican Airlines
א' 6/308:30 amORD - EYW
1 stop6h 59mAmerican Airlines
Deal found 5/14$670
ה' 6/2012:46 pmEYW - ORD
2 stops9h 10mAmerican Airlines
ב' 6/246:01 amORD - EYW
2 stops9h 28mAmerican Airlines
Deal found 5/14$675
ה' 6/2712:46 pmEYW - ORD
2 stops9h 10mAmerican Airlines
א' 6/306:31 amORD - EYW
2 stops11h 28mAmerican Airlines
Deal found 5/14$677
ד' 11/61:31 pmEYW - ORD
2 stops9h 20mAmerican Airlines
א' 11/105:29 amORD - EYW
2 stops6h 31mAmerican Airlines
Deal found 5/14$1,725
ה' 6/2011:15 amEYW - ORD
2 stops9h 15mAmerican Airlines
ב' 6/246:31 amORD - EYW
2 stops8h 58mAmerican Airlines
Deal found 5/14$1,727
Cheap Key West to Chicago flights in May & June 2024
Find cheap flight options from Key West to Chicago specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Prices were last updated on מאי 14, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
ה' 6/277:25 amEYW - ORD
1 stop4h 47mDelta
א' 6/306:00 amORD - EYW
1 stop6h 20mDelta
Deal found 5/14$313
ה' 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
ה' 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$339
ה' 6/204:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
ב' 6/245:01 amORD - EYW
1 stop7h 54mAmerican Airlines
Deal found 5/14$347
ה' 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
ה' 6/1312:22 pmORD - EYW
1 stop6h 18mDelta
Deal found 5/14$363
ה' 6/610:04 amEYW - ORD
3 stops15h 51mMultiple Airlines
ה' 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$371
ה' 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
ה' 6/135:34 pmORD - EYW
3 stops21h 34mMultiple Airlines
Deal found 5/14$401
ד' 5/2211:43 amEYW - ORD
1 stop6h 04mDelta
א' 5/2612:31 pmORD - EYW
1 stop6h 09mDelta
Deal found 5/13$428
ה' 6/610:04 amEYW - ORD
3 stops15h 51mMultiple Airlines
ה' 6/135:34 pmORD - EYW
3 stops21h 34mMultiple Airlines
Deal found 5/14$433
ב' 5/206:10 pmEYW - ORD
1 stop6h 49mAmerican Airlines
ב' 5/275:15 amORD - EYW
1 stop4h 46mAmerican Airlines
Deal found 5/14$435
Key West to Chicago 2024 flight deals
Discover exclusive flight deals for travel between Key West and Chicago in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
These are some of the best deals we've found on flights to Chicago in 2024 at this time. Check back soon for alternative fares.
ד' 11/64:00 pmEYW - ORD
Nonstop3h 24mUnited Airlines
א' 11/1010:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/14$229
ו' 9/276:05 pmEYW - MDW
1 stop4h 39mDelta
ג' 10/110:11 amMDW - EYW
1 stop5h 58mDelta
Deal found 5/13$232
ד' 11/61:00 pmEYW - ORD
1 stop9h 23mUnited Airlines
א' 11/1010:40 amORD - EYW
Nonstop3h 10mUnited Airlines
Deal found 5/14$259
ג' 12/241:44 pmEYW - ORD
Nonstop3h 31mAmerican Airlines
ש' 1/115:20 amORD - EYW
1 stop4h 57mAmerican Airlines
Deal found 5/14$292
ה' 6/277:25 amEYW - ORD
1 stop4h 47mDelta
א' 6/306:00 amORD - EYW
1 stop6h 20mDelta
Deal found 5/14$313
ה' 6/65:09 pmEYW - ORD
2 stops25h 31mMultiple Airlines
ה' 6/138:04 pmORD - EYW
1 stop11h 58mMultiple Airlines
Deal found 5/14$339
ד' 11/63:16 pmEYW - ORD
1 stop5h 17mAmerican Airlines
א' 11/107:00 amORD - EYW
1 stop7h 09mAmerican Airlines
Deal found 5/14$345
ה' 6/204:59 pmEYW - ORD
1 stop7h 59mAmerican Airlines
ב' 6/245:01 amORD - EYW
1 stop7h 54mAmerican Airlines
Deal found 5/14$347
ה' 6/66:10 pmEYW - ORD
1 stop6h 44mDelta
ה' 6/1312:22 pmORD - EYW
1 stop6h 18mDelta
Deal found 5/14$363
Key West to Chicago flights leaving soon
Find last-minute flight options from Key West to Chicago for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Book one of these great deals on flights from Key West to Chicago. To prevent any unwanted surprises, users should verify their flight info before booking.
ד' 5/2211:43 amEYW - ORD
1 stop6h 04mDelta
א' 5/2612:31 pmORD - EYW
1 stop6h 09mDelta
Deal found 5/13$428
ב' 5/206:10 pmEYW - ORD
1 stop6h 49mAmerican Airlines
ב' 5/275:15 amORD - EYW
1 stop4h 46mAmerican Airlines
Deal found 5/14$435
ד' 5/227:05 amEYW - ORD
2 stops14h 06mDelta
א' 5/2612:31 pmORD - EYW
1 stop6h 09mDelta
Deal found 5/13$586
ב' 5/2011:45 amEYW - ORD
1 stop28h 08mUnited Airlines
ב' 5/276:30 amORD - EYW
2 stops12h 05mUnited Airlines
Deal found 5/14$614
ב' 5/2011:45 amEYW - ORD
2 stops9h 40mUnited Airlines
ב' 5/276:30 amORD - EYW
2 stops12h 05mUnited Airlines
Deal found 5/14$778
One-way flights to Chicago from Key West
Search for one-way flight options from Key West to Chicago. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Take a look at some of the best available options we've come across on one-way flights from Key West to Chicago. For those needing a return trip from Key West, there is a search form available above.
ג' 6/2511:20 amEYW - ORD
1 stop28h 32mUnited Airlines
Deal found 5/14$207
א' 8/1811:20 amEYW - ORD
1 stop23h 31mUnited Airlines
Deal found 5/14$217
ו' 9/1311:45 amEYW - ORD
1 stop23h 06mUnited Airlines
Deal found 5/14$225
א' 7/212:43 pmEYW - ORD
2 stops19h 40mMultiple Airlines
Deal found 5/14$247
ג' 6/116:00 pmEYW - MDW
1 stop4h 46mDelta
Deal found 5/12$254
א' 11/1011:45 amEYW - ORD
1 stop23h 02mUnited Airlines
Deal found 5/14$255
א' 6/211:45 amEYW - ORD
1 stop22h 36mUnited Airlines
Deal found 5/13$257
א' 7/211:44 pmEYW - ORD
1 stop7h 40mAmerican Airlines
Deal found 5/14$259
ו' 9/136:01 pmEYW - ORD
2 stops6h 35mAmerican Airlines
Deal found 5/14$264
Find flights from Key West to Chicago within your budget
Customize your flight search to find flights from Key West to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Fly from
Any airport
Fly to
Any airport
Budget
$229 - $371
Route
Depart
Return
Price
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ד' 11/6
Nonstop3h 24m
Chicago O'Hare Intl
א' 11/10
Nonstop3h 10m
$229
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
ו' 9/27
1 stop4h 39m
Chicago Midway
ג' 10/1
1 stop5h 28m
$232
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ד' 11/6
1 stop9h 23m
Chicago O'Hare Intl
א' 11/10
Nonstop3h 10m
$259
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ה' 6/27
1 stop4h 47m
Chicago O'Hare Intl
א' 6/30
1 stop6h 20m
$313
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ה' 6/6
2 stops25h 31m
Chicago O'Hare Intl
ה' 6/13
1 stop11h 58m
$339
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ד' 11/6
1 stop5h 17m
Chicago O'Hare Intl
א' 11/10
1 stop7h 09m
$345
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ה' 6/20
1 stop7h 59m
Chicago O'Hare Intl
ב' 6/24
1 stop7h 54m
$347
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ה' 6/6
1 stop6h 44m
Chicago O'Hare Intl
ה' 6/13
1 stop6h 18m
$363
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
ה' 6/6
3 stops15h 51m
Chicago O'Hare Intl
ה' 6/13
1 stop11h 58m
$371
When is the cheapest time to fly from Key West to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Key West to Chicago. Price data was last updated on May 12, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Key West to Chicago flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Average price of flights to Chicago by month
Plan your trip from Key West to Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Key West to Chicago is currently $243 while a round-trip flight costs $311. Price data was last updated on May 12, 2024.
Currently, February is the cheapest month in which you can book a flight from Key West to Chicago (average of $244). Flying from Key West to Chicago in June is currently the most expensive (average of $342). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$248
February
$244
March
$280
April
$258
May
$278
June
$342
July
$327
August
$274
September
$258
October
$248
November
$270
December
$248
Temperature and rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.
CHI Temperature | 23 - 73.4 °F |
|---|
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated מאי 14, 2024.
Read reviews from past customers who have flown United Airlines, American Airlines and Delta from Key West to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
9,152 reviews
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,706 reviews
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
1,020 reviews
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
10,959 reviews
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
14,561 reviews
9,152 reviews
Boarding
8.2
Crew
8.6
Overall
8.1
Comfort
7.9
Entertainment
7.3
Food
7.3
Reviews
1 / 10
Paid a lot for our exit row seats and they weren’t that roomy.
Related info for your journey
Find useful and relevant information for your journey from Key West to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Key West to ChicagoSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Key West to Chicago
Discover the top 3 airlines that operate flights from Key West to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,632,958 searches. Data last updated מאי 14, 2024.
Search flights from Key West to Chicago by cabin class
Find flights from Key West to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Weekly flight availability from Key West to Chicago
Explore weekly flight availability from Key West to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated מאי 14, 2024.
| Sunday | 3daily flights |
|---|---|
| Monday | 3daily flights |
| Tuesday | 3daily flights |
| Wednesday | 3daily flights |
| Thursday | 3daily flights |
| Friday | 3daily flights |
| Saturday | 3daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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Users can book flights with no change fees policies with our dedicated filters. Book flights from Key West to Chicago flexibly with Cheapflights today.
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